If you had asked my classmates in high school if they thought I would someday be in charge of picking the Coolest Person of the Year, they would have said, “You mean in charge of sitting all alone in his house typing about a famous person he doesn’t know? That sounds about right.”

But they would be wrong. In fact, the Coolest Person franchise, which is the kind of attention-grabbing journalistic endeavor you’d think would get someone a raise, is now officially a group endeavor. To pick the 2012 winner, I assembled what I call the League of the Year, which consists of people who were named the most something of the year. It is by definition the most superlative group ever assembled, and it’s now at my disposal. The devil wants to bowl me for my soul? I’ve got Bowler of the Year ESPY winner Sean Rash. I need to solve a quadratic equation? I’ll call National Teacher of the Year Rebecca Mieliwocki. A kid bails on a playdate with my son? I’ll just e-mail Playmate of the Year Jaclyn Swedberg.

The only miscalculation I made was not realizing experts tend not to be the broadest thinkers. When I asked whom they thought I should anoint Coolest Person, league member and Thrasher magazine Skater of the Year Danny Gonzalez suggested skateboarder Louie Lopez. Cosmopolitan’s Bachelor of the Year, Cleveland reporter Chris Van Vliet, chose Channing Tatum, People’s Sexiest Man Alive. Air Guitar world champion Justin “Nordic Thunder” Howard suggested party-anthem rocker Andrew W.K. Laura James, winner of America’s Next Top Model, nominated herself.

Worse, most of the league members were unfamiliar with the people I was considering, including R&B singer Frank Ocean, Newark Mayor Cory Booker and comedian Louis CK. Though College Photographer of the Year Magnus Holm did suggest Louis CK. And Mieliwocki mentioned Booker as well as Barack Obama, whom I was also considering. Of course, her main choice was “teachers.” I was starting to understand how the Nobel Committee wound up giving the 2012 Peace Prize to Europe.

So after politely thanking the league for its suggestions, I basically—yes, you jerks from high school—just sat alone at home and picked a celebrity. The 2012 Coolest Person of the Year is a woman who was unafraid to showcase her flaws. A woman who wore less makeup on TV than in real life and purposely shot herself naked in more unflattering ways than a blackmailer would. A woman whose entire persona is based on doing the wrong thing yet who reportedly got a $3.7 million advance for an advice book. A woman who made an Obama campaign video centering on a double entendre about losing her virginity to the President. A woman who was nominated for four Emmys and, far cooler, zero People’s Choice Awards. A woman who responded to 2010 Coolest Person James Franco’s harsh Huffington Post essay criticizing Girls, the HBO show she created and stars in, by saying she’s a big James Franco fan.

Lena Dunham might lack swagger and mystery. But she ushers in a second-generation cool for the oversharing era. “She doesn’t care what you think of her,” says Judd Apatow, an executive producer of Girls. “O.K., she does care. A lot. But she won’t change who she is to please you.” And she tempers her uncool puppy-dog eagerness with an insouciance that comes from knowing you will never, ever be as traditionally cool as your avant-garde New York City artist parents.

Unlike past Coolest winners who chose either not to talk about it (2011’s Ryan Gosling) or to say cool, cryptic things about it like “I invest my emotions into how well I think the things have been rendered” (2010’s Franco), Dunham didn’t hide her excitement. She emailed, “Wow, that is—for lack of a better word—really cool. What an honor. Will I get in any Web trouble for being genuinely, unsnarkily excited to be the first woman to win Joel Stein’s Coolest Person of the Year?”

Yes, Lena, you will. But you will do it anyway, on Twitter and hopefully in an even larger public forum, like Letterman or a magazine cover profile. Because—just like the many other women who have been considered not funny enough, not tough enough, not Supreme Court–y enough, not Augustay enough or not capable of following the complicated no-turn-on-red laws of Saudi Arabia enough—you have broken a barrier. And the only way you can help more women do the same is to keep talking about this honor and, more important, the cool guy who bestowed it upon you.